Diacyl acrylamide and its



Patented May 25,1943

UNITED IS PATENT F CE. A

Y "maornaciima Ann rrs v Q I PREPARATION Joy G. Lichty, Stow, Ohio. assignor to Wingfoot Corporation, Akron, 0hio, a corporation of Del-- No'Drawin'g. Application July 22, 1942,

- Serial No. 451,944, J

50mins. (Cl. 260-561) This invention relates to-the preparation of diacyl acrylamides'and to the product so prepared. This application is in part a continuation of my application Serial No. 314,634, filedJanuary 19, 1940.

According to the process of this invention, the

diacyl acrylamides are prepared by reacting with a carboxylic acid anhydride an acrylonitriie of the general formula CHa:CX.CN where Xdesignates hydrogen, halogen or an alkyl, monovalent alkylene or aryl group.

Among the acrylonitriles which may be used in i the reaction are acrylonitrlle, methacrylonitrile,

ethacrylonitrile, propylacrylonitrile and other alpha 'alkyl acrylorrltriles, phenyl acrylonitrile,

vinyl 'acrylonitrile, chloroacrylonitrile, and bromoacrylonitrile,etc.

temperatures both below and above these limits may sometimes be used, superatmo'spheric pres sure being incidentally generated atthe hi'gher temperatures, since a closedvessel, such as'an; autoclave, must be employed'toconflne the-refaction.

. The process may be illustrated by the renewing example:

oyed, although these proportions may be varied,

dissolved in acetone and precipitated in alcohol to give a solid which melted in part at 195 C.

The reaction 'is illustrated by the following equationi The above process may readilybeapplied to the reaction of'other acrylonitriles with other anhydrides. The compounds obtained are diaeyl acrylamide of'the general formula:

CH2: CX.CO.N(CO.R) a

in which X designates hydrogen or halogen or,

an alkyl, monovalent .alkylene or aryl radical and R, designates an alwl or aryl radical.

Copolymers of diacyl arcrylamides andthelr preparation are covered in my companion application Serial No. 451,945, filed July 22, 1942.

What I claim is:

1. The-method, of preparing a diacyl acrylamide whichcomprises reacting under heat a carboxylic acid anhydride with an 'acrylonitrile of the formula CHuCXCN in which x is selected from the group consisting of hydrogen, halogen, an alkyl, vinylacrylonitrile and phenyl acrylov nitrile, to combine the same in equimolecular proportions.

2."The method of preparing diacetyl' methacrylamide which comprises reacting under heat l methacrylonitrile with acetic'anhydride to combine the same in equimolecular proportions.

3. The method of preparing a diacyl acrylamide which comprises reacting at a temperature oi about 100 to 250 in approximately .equlmolecular proportions a carboxylic acid anhydride and an acrylonitrile having the formula A solution of 41 cc. of methacrylonitrile'and 4'7 cc. of acetic anhydride was sealed'in a glass tube and heated to 200 C. in an electric furnace for 2% hours. Upon cooling there was obtaineda yellow liquid containing a gel. The gel was CHaCXCN in which X is selected from the group consisting of hydrogen, halogen, alkyl, vinyl acrylonitrile and phenyl acrylonitrile..

4. A diacyl acrylamide. 5. 'Diacetyl methacrylamide.

- JOY G. LICHTY. 

